If you're looking to househack again, then the conventional 5% down is a very viable alternative to the 3.5% down FHA option. 

That's not exactly a good alternative to sub to. 

Another good alternative would be Bonita Springs, just on the North side of Naples, or Cape Coral as I mentioned above

If you added in the cash you should have to protect against contingencies, the actual return goes down (or the risk sykrockets, your choice)- If the $300K properties cashflow, definitely a better bet. 

But there are alternative exits that still profit a decent amount, in my opinion anyways.So, this is what you would call a high risk strategy? 

Mostly people with minimal RE experience are adding a single ADU and they often make that choice based on cash flow without taking into account the negative equity position.  

Are you saying this would be a good alternative to Pace Morby's Sub To program?

If so, I'd 1) join a real estate investing mastermind that focuses on your asset class of choice (multifamily, industrial, storage, etc.) and learn as much as I could - it's worth the $10k-$20k in both knowledge and connections.

Artwork is often personal choice, but you definitely need some stuff there.

After talking with an operator I felt he was a good choice for a tenant and he mad a great offer above market for the apartment so we agreed.In the past I would usually rent my own units and to stay competitive I would keep an eye on the rentals in the area and try to be one step above if I could....This time that was a little tougher as the neighborhood hasn't gotten very trendy.